Playboy X

Trey "Playboy X" Stewart (1983-2008) was the acting boss of the North Harlem Hustlers street gang in Harlem, New York City from 2004 to 2008 while his boss Dwayne Forge was incarcerated on drug charges. Playboy X was involved with the cocaine distribution racket in northern Manhattan during the 2000s, and he monitored several of the city's major drug deals, becoming an associate of Puerto Rican drug baroness Elizabeta Torres in the South Bronx. Playboy modernized the gang, investing in both illegal and legitimate businesses; he made peace with the rival Spanish Lords gang by giving them control of the Triangle Club strip club. He was murdered by Forge in 2008 after he attempted to have the freed Forge murdered so that he could continue being gang leader.

Early life
Trey Stewart was born in Harlem, Manhattan, New York City in 1983, and he was a smart child. However, he had no street knowledge as a youth, and he was taken under the wing of drug dealer Dwayne Forge, who taught him the rules of the streets and became a father figure to him. Stewart once worked as a robber before moving into the cocaine distribution business, and he became known as "Playboy X", taking the "X" from "Xenotime Street", the location of his penthouse. When Forge was arrested in 1999, the young Playboy was encouraged to become the new acting leader of the gang, and he would stop visiting Forge in prison in 2004, becoming a selfish person due to his belief that the gang would have to adapt to modern times.

Rise and fall
Playboy became the boss of the North Harlem Hustlers gang, and he would modernize the gang, allying with Puerto Rican drug baroness Elizabeta Torres in The Bronx and with the Spanish Lords gang. Playboy X sold the Triangle Club to the Spanish Lords to make some money, and he bought a gold-colored SUV and a beautiful penthouse. Playboy almsot forgot that Forge was the real boss, and he became the overseer of several major drug deals in the city; in 2008, he befriended United Arab Emirates real estate developer Yusuf Amir and Serbian criminal Niko Bellic, hiring Bellic to help him with killing some rivals and with helping the construction of Amir's new building in Battery Park City. When Forge was released from prison, Forge reversed several of Playboy's gains, killing the leaders of the Spanish Lords gang at the Triangle Club. Playboy would ask Bellic to help him with killing Forge, but Forge hired Bellic to kill Playboy, and Bellic sided with Forge, who reminded him of himself. Bellic confronted Playboy at his penthouse and killed him after a shootout with his bodyguards.